Cyclopentanon

Cyclopentanone

HCID 8452CAS 120-92-3

Grundinformationen

Standard-SMILES
O=C1CCCC1
InChIKey
BGTOWKSIORTVQH-UHFFFAOYSA-N
Summenformel
C5H8O
Durchschnittliche Molmasse
84,12 g/mol
Monoisotopische Masse
84,05751488

Überblick

Cyclopentanone appears as a clear colorless liquid with a petroleum-like odor. Flash point 87 °F. Less dense than water and insoluble in water. Vapors heavier than air.

Namen und Bezeichner

Bevorzugter Name
Cyclopentanone
IUPAC
cyclopentanone
Lokaler Name
Cyclopentanon
Englischer Name
Cyclopentanone
Summenformel
C5H8O
Molmasse
84.12

Namen und Synonyme

CYCLOPENTANONE120-92-3Adipic ketoneKetocyclopentaneKetopentamethyleneDumasinAdipinketonAdipin ketonDTXSID3029154220W81TN3SNSC-4122DTXCID209154
Weitere Namen anzeigen
CyclopentanonCyclopentanone-HGFEMA 3910opentanone
FEMA NO. 3910CHEBI:16486RefChem:5722204-435-9cyclopentan-1-oneoxocyclopentaneNSC 4122MFCD00001409

Datenbank-Bezeichner

CAS
120-92-3
PubChem CID
8452
DTXSID
DTXSID3029154
ChEMBL
CHEMBL18620
ChEBI
CHEBI:16486
UNII
220W81TN3S
EC Number
204-435-9
Nikkaji
J5.333C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,4
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
6

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Ketones (<C12)
SpringerMaterials PropertiesSchoenflies notation
LogP0.38
OdorDISTINCTIVE ETHEREAL ODOR, SOMEWHAT LIKE PEPPERMINT
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Physikochemische Eigenschaften

Schmelzpunkt
-51 °C · -51 °C (lit.)
Siedepunkt
130 · 130-131 °C (lit.)
Dichte
0.951 g/mL · 0.951 g/mL at 25 °C (lit.)
Dampfdichte
2.97 · 2.97 (vs air)
Dampfdruck
11.5 hPa · 11.5 hPa (20 °C)
FEMA
3910 · 3910 | CYCLOPENTANONE

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P264, P264+P265, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.8% (12 of 678) of reports.

Warning

H226 (98.2%): Flammable liquid and vapor [Warning Flammable liquids]

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Cyclopentanone

Regulation (EC) No 1334/2008 (amended)

Cyclopentanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclopentanone are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 29-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13920

Cyclopentanone: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Cyclopentanone: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Heating will cause rise in pressure with risk of bursting. Gas/air mixtures are explosive.

Fire PotentialDANGEROUS WHEN EXPOSED TO FLAME; CAN REACT WITH OXIDIZING MATERIALS.
Health Hazards · 2 Einträge

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 3 Einträge

Fresh air, rest. Refer for medical attention.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

Safe StorageFireproof. Separated from acids. Cool. Keep in the dark. Keep in a well-ventilated room. Store only if stabilized.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Cyclopentanone is not expected to hydrolyse in soils(1), or undergo photolysis on sunlit soil surfaces due to lack of >290 nm UV adsorption(2). A single 5-day BOD screening test, which utilized activated sludge for inocula, suggests that cyclopentanone will biodegrade rapidly upon acclimation in terrestrial environments(3). An estimated Koc of 30(1) indicates cyclopentanone should have a very high mobility in soil(4). A Henry's Law constant of 1.0X10-5 atm-cu m/mole(5) suggests volatilization of cyclopentanone from moist soils may be an important fate process(1). Based on a vapor pressure of 11.4 mm Hg at 25 °C(6), cyclopentanone should evaporate from dry surfaces, especially when present in high concn such as in spill situations(SRC).

AQUATIC FATE: Cyclopentanone is not expected to hydrolyze(1) or undergo direct photolysis in aquatic systems(2). A single 5-day BOD screening test, which utilized activated sludge for inocula, suggests that cyclopentanone will biodegrade rapidly upon acclimation in natural waters(3). An estimated log bioconcentration factor (log BCF) of -0.05(1) indicates cyclopentanone should not bioconcentrate in aquatic organisms(SRC). An estimated Koc of 30(1) indicates cyclopentanone should not partition from the water column to organic matter contained in sediments and suspended solids(SRC). A Henry's Law constant of 1.0X10-5 atm-cu m/mole at 25 °C(4) indicates that volatilization of cyclopentanone from natural bodies of water should be an important fate process(1). Based on this Henry's Law constant, the volatilization half-life from a model river has been estimated to be 3.5 days(1,SRC). The volatilization half-life from an model pond, which considers the effect of adsorption, has been estimated to be about 40 days(5,SRC).

ATMOSPHERIC FATE: Based on a vapor pressure of 11.4 mm Hg at 25 °C(1), cyclopentanone is expected to exist almost entirely in the vapor phase in ambient air(2). Vapor phase reactions with photochemically produced hydroxyl radicals in the atmosphere have been shown to be important(SRC). A rate constant for cyclopentanone of 2.94X10-12 cu cm/molecule-sec at 25 °C corresponds to an atmospheric half-life of about 5.5 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(3). Direct photolysis in air is not expected to be an important environmental fate process(4).

Food Survey ValuesCyclopentanone was identified as a volatile component of baked potatoes produced by the baking process(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.
Signs and Symptoms · 3 Einträge

Cough. Sore throat.

Redness. Pain.

Redness. Pain.

Effluent Concentrations · 1 Eintrag

Cyclopentanone was detected in 4 of 7 wastewater effluents from energy related processes(1). A groundwater water sample from a coal gasification facility in Hanna, WY contained cyclopentanone at an average concn of 32 ppb; the process water at a coal gasification facility in Gillette, WY contained cyclopentanone at an average concn of 110 ppb; effluent from the gasification of Rosebud coal in Morgantown, WV contained cyclopentanone at an average concn of 56 ppb; and retort water from an in situ shale oil processing facility in Rock Spring, WY contained cyclopentanone at an average concn of 5 ppb(1). Wastewater from coal gasification at the Grand Fork's Energy Technology Center, ND was also reported to contain cyclopentanone at a concn of 0.8 mg/L(2). In addition, wastewater effluent from a shale oil facility in Queensland, Australia was shown to contain cyclopentanone at a concn of 53 mg/L(3).

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 2245
hs_code
2914 29 00
RTECS-Nr.
GY4725000
risk_code
10-36/38

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

... MINOR (1-2%) METABOLITES OF CYCLOPENTANONE ... HAVE BEEN DETECTED IN RAT & RABBIT URINE. 2-HYDROXYCYCLOALKYLMERCAPTURIC ACIDS ... WHICH WERE PRESENT AS ... SULFATE ('DOUBLE CONJUGATE') ... PRESUMABLY FORMED BY DEHYDRATION OF CYCLOALKANOLS (MAJOR METABOLITES) TO CYCLOALKENES WITH SUBSEQUENT EPOXIDATION & MERCAPTURATION.

... RABBITS FED ... /CYCLOPENTANONE/ EXCRETED LARGE AMT (MORE THAN HALF THE DOSE) AS CYCLOPENTYL ... GLUCURONIDE ... MINOR AMT OF SULFATE CONJUGATES WERE ALSO PRESENT.

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 2 Einträge

Used as intermediate for pharmaceuticals, biologicals, insecticides, and rubber chemicals; [Hawley]

INT FOR PHARMACEUTICALS, BIOLOGICALS, INSECTICIDES, & RUBBER CHEMICALS.

U.S. Imports(1983) 2.00X10+5 g
U.S. Production2023: 5,500,000 - <7,000,000 lb
Consumer UsesFragrance
Industry UsesSolvent
Methods of ManufacturingPREPD BY HEATING ADIPIC ACID TO 285-295 °C IN PRESENCE OF BARIUM HYDROXIDE, DISTILLING, EXTRACTING WITH ETHER & FRACTIONATING.
Anwendungen · 2 Einträge

OccurrenceReported found in roasted onion, baked potato, tomato, gruyere cheese, butter, heated chicken, boiled beef, heated pork, roasted pecan, yellow passion fruit juice.

VerwendenCyclopentanone is used as an intermediate in the synthesis of rubber adhesives, synthetic resins, pharmaceuticals and biologically active compounds. It acts as precursor for the preparation of cyclopentamine and also pentethylcyclanone, cyclopentobarbital. It is a useful laboratory reagent and is used as thinner for epoxies. It can also be used as a solvent in paint and varnish removers and for electronic applications. As a dry cleaning agent, it is used for oil extraction. It is also involved in the preparation of cyclopentanone derivatives like cyclopenylamine and cyclopentanol which find application in the perfume industry.

Darstellung

synthetischePrepared by heating adipic acid (285 to 295°C) in the presence of barium hydroxide, distilling, ether extraction and then fractionation.

Anbieter50 Anbieter

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爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A cyclic ketone that consists of cyclopentane bearing a single oxo substituent.

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